2.0 2012-07-30 14:54:55 -0600 2015-06-03 17:20:52 -0600 ECMDB21206 M2MDB001614 Dihydroneopterin monophosphate Dihydroneopterin monophosphate is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Dihdroneopterin monophosphate is an intermediate involved in tetrahydrofolate biosynthesis and salvage in E. coli. It is converted to 7,8-dihydroneopterin through an unknown phosphorylase enzyme. 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate 2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphoric acid 7,8-Dihydro-D-neopterin 3'-phosphate 7,8-dihydro-D-Neopterin 3'-phosphoric acid Dihydroneopterin 3'-monophosphate Dihydroneopterin 3'-monophosphoric acid Dihydroneopterin 3'-phosphate Dihydroneopterin 3'-phosphoric acid Dihydroneopterin monophosphoric acid Dihydroneopterin-P C9H12N5O7P 333.1946 333.047434275 6-[(1S,2R)-3-(hydrogen phosphonatooxy)-1,2-dihydroxypropyl]-2-imino-1,2,7,8-tetrahydropteridin-4-olate 6-[(1S,2R)-3-(hydrogen phosphonatooxy)-1,2-dihydroxypropyl]-2-imino-7,8-dihydro-1H-pteridin-4-olate [H][C@@](O)(COP(O)([O-])=O)[C@@]([H])(O)C1=NC2=C(NC1)NC(=N)N=C2[O-] InChI=1S/C9H14N5O7P/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-21-22(18,19)20/h4,6,15-16H,1-2H2,(H2,18,19,20)(H4,10,11,13,14,17)/p-2/t4-,6+/m1/s1 PLSQMGZYOGSOCE-XINAWCOVSA-L Cytosol logp -1.69 ALOGPS logs -2.05 ALOGPS solubility 3.29e+00 g/l ALOGPS logp -5.8 ChemAxon pka_strongest_acidic -13 ChemAxon pka_strongest_basic 15.08 ChemAxon iupac 6-[(1S,2R)-3-(hydrogen phosphonatooxy)-1,2-dihydroxypropyl]-2-imino-1,2,7,8-tetrahydropteridin-4-olate ChemAxon average_mass 333.1946 ChemAxon mono_mass 333.047434275 ChemAxon smiles [H][C@@](O)(COP(O)([O-])=O)[C@@]([H])(O)C1=NC2=C(NC1)NC(=N)N=C2[O-] ChemAxon formula C9H12N5O7P ChemAxon inchi InChI=1S/C9H14N5O7P/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-21-22(18,19)20/h4,6,15-16H,1-2H2,(H2,18,19,20)(H4,10,11,13,14,17)/p-2/t4-,6+/m1/s1 ChemAxon inchikey PLSQMGZYOGSOCE-XINAWCOVSA-L ChemAxon polar_surface_area 205.74 ChemAxon refractivity 100.97 ChemAxon polarizability 27.1 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge -2 ChemAxon Folate biosynthesis The biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate. Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate. This product goes on to a one carbon pool by folate pathway. PW000908 ec00790 Metabolic GTP degradation GTP, produced in the nucleotide de novo biosyntheis pathway, interacts with a water molecule through a GTP cyclohydrolase resulting in a formate, hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound interacts with a water molecule through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, a hydrogen ion and a 7,8-dihydroneopterin 3'-phosphate. The latter compound interacts with water spontaneously resulting in the release of a phosphate and a 7,8 dihydroneopterin. The latter compound interacts with a dihydroneopterin aldolase resulting in the release of a glycolaldehyde and a 6-hydroxymethyl-7,8-dihydropterin. This compound then is then diphosphorylated by reacting with a ATP driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in the release of a hydrogen ion, an AMP and 6-hydroxymethyl-7,8-dihydropterin diphosphate. GTP interacts with a cyclic pyranopterin monophosphate synthase resulting in the release of a diphosphate and a cyclic pyranopterin phosphate. The latter compound interacts with a thiocarboxylated small subunit of molybdopterin synthase (a protein) and a water molecule through a molybdopterin synthase resulting in the release of 4 hydrogen ions, 2 small subunits of molybdopterin synthase and a molybdopterin. The molybdopterin interacts with an ATP and a hydrogen ion through a molybdopterin adenylyltransferase resulting in the release of a diphosphate and a molybdopterin adenine dinucleotide. PW001888 Metabolic 6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147 Specdb::NmrOneD 334838 Specdb::NmrOneD 334839 Specdb::NmrOneD 334840 Specdb::NmrOneD 334841 Specdb::NmrOneD 334842 Specdb::NmrOneD 334843 Specdb::NmrOneD 334844 Specdb::NmrOneD 334845 Specdb::NmrOneD 334846 Specdb::NmrOneD 334847 Specdb::NmrOneD 334848 Specdb::NmrOneD 334849 Specdb::NmrOneD 334850 Specdb::NmrOneD 334851 Specdb::NmrOneD 334852 Specdb::NmrOneD 334853 Specdb::NmrOneD 334854 Specdb::NmrOneD 334855 Specdb::NmrOneD 334856 Specdb::NmrOneD 334857 Specdb::MsMs 29126 Specdb::MsMs 29127 Specdb::MsMs 29128 Specdb::MsMs 35684 Specdb::MsMs 35685 Specdb::MsMs 35686 25245170 26331350 C05925 58762 DIHYDRONEOPTERIN-P Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Dihydroneopterin triphosphate pyrophosphatase P0AFC0 NUDB_ECOLI nudB http://ecmdb.ca/proteins/P0AFC0.xml Mutator mutT protein P08337 MUTT_ECOLI mutT http://ecmdb.ca/proteins/P08337.xml Dihydroneopterin triphosphate + Water > Dihydroneopterin monophosphate + Hydrogen ion + Pyrophosphate H2NEOPTERINP3PYROPHOSPHOHYDRO-RXN Dihydroneopterin monophosphate + Water > 7,8-Dihydroneopterin + Phosphate DIHYDRONEOPTERIN-MONO-P-DEPHOS-RXN 7,8-dihydroneopterin 3'-triphosphate + Water > Pyrophosphate + Hydrogen ion + Dihydroneopterin monophosphate PW_R003397